Kid-friendly holiday rentals in Sheffield
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Sheffield
Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sheffield kid-friendly rentals
Child-friendly house rentals
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
15–22 Oct
Home in Egremont
4.93 out of 5 average rating, 256 reviewsModern Farm House 5 minutes from Great Barrington
8–15 Apr
Home in Great Barrington
4.96 out of 5 average rating, 214 reviewsJaw dropping mountain & lake views
17–24 Nov
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
13–20 Mar
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
17–24 Aug
Home in Great Barrington
4.95 out of 5 average rating, 114 reviewsThe Hideaway: Berkshire Home - village of Egremont
6–13 Oct
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
4–11 Jan
Home in Millerton
4.96 out of 5 average rating, 115 reviewsVacation Home In Millerton
5–12 Mar
Kid-Friendly apartment rentals
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
20–27 Dec
Apartment in Great Barrington
4.95 out of 5 average rating, 131 reviewsGB Eclectic Victorian
27 Oct – 3 Nov
Apartment in Millerton
4.8 out of 5 average rating, 231 reviewsGardens Galore and Village Whimsy Retreat
23 Feb – 2 Mar
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
19–26 Oct
Apartment in Hudson
4.95 out of 5 average rating, 100 reviewsRestored 19th century farm house apartment
4–11 Nov
Apartment in Plainfield
4.97 out of 5 average rating, 238 reviewsSunny, light filled loft in 1873 Colonial
9–16 Mar
Apartment in Petersburg
4.85 out of 5 average rating, 149 reviewsThe Beer Diviner Brewery Apartment
10–17 Sep
Apartment in Winchester
4.91 out of 5 average rating, 340 reviewsGateway to the Berkshires
28 Apr – 5 May
Child-Friendly Holiday Condos
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
2–9 Nov
Condo in Poughkeepsie
4.97 out of 5 average rating, 224 reviewsSpacious and stylish entire one bedroom apartment.
24 Jun – 1 Jul
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @Jiminy Peak
6–13 Nov
Condo in Kingston
4.91 out of 5 average rating, 105 reviewsCozy home walking distance to cafés & waterfront
20–27 Sep
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
19–26 Sep
Condo in New Britain
4.87 out of 5 average rating, 39 reviewsBeautiful Space All For You!
2–9 Sep
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
3–10 Aug
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
30 Nov – 7 Dec
Quick stats about holiday rentals that are kid-friendly in Sheffield
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
$204 NZD before taxes and fees
Destinations to explore
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- Family-friendly rentals Sheffield
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